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Photocatalytic Generation of Nitrenes for Rapid Diaziridination

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posted on 21.10.2017, 00:00 by Ramij R. Mondal, Saikat Khamarui, Dilip K. Maiti
A blue LED, an organic photocatalyst (rose bengal), and the Lewis acid like oxidant PhI­(OAc)2 were utilized to generate nitrene intermediates through reactions of 1,2-diols and aliphatic amines under mild reaction conditions. A versatile and rapid diaziridination strategy was established to construct functionalized 1,2-disubstituted diaziridines, diaziridines with chiral substituents, and 1,2,3-trisubstituted analogues with excellent reaction rates, yields, and stereoselectivities. Control and labeling experiments to elucidate the mechanism of this elegant metal-free photocatalyzed cyclization reaction were performed.